


I Like To Watch 2

by JackTrades



Series: I Like To Watch [2]
Category: Supernatural
Genre: Animated GIFs, Cunnilingus, Explicit Sexual Content, F/M, M/M, Masturbation, NSFW Art, PWP, Plot What Plot/Porn Without Plot, Vaginal Fingering, Voyeurism
Language: English
Status: Completed
Published: 2015-04-27
Updated: 2015-04-27
Packaged: 2018-03-26 00:13:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,238
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3830050
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Dean picks up a girl to have sex while Sam watches</p>
            </blockquote>





	I Like To Watch 2

**Author's Note:**

> This is a sequel to I Like To Watch. You don't need to read it to understand the events of this shameless smut.

Several months had passed since that fateful day when Dean was jerking off only to have Sam walk in on him.  Having Sam and his lady-for-the-night ask him to stay and watch was, by far, the most awesome surprise of his life. Now it was late April and almost Sam’s birthday.  Dean could think of no better way to give him a birthday present and repay the favor than to finally find a girl to fuck and let Sam watch.  He would have done it much sooner, but had not quite found a girl that was right yet.  She had to be the right mix of willing, adventurous, and hot enough to be a treat for Sam… perhaps he was over thinking it.  He shouldn’t be so fixated on making it good for Sam, but he was. They hadn’t really talked about it.  Dean tried to make a passing comment about how he thought Sam’s roughness in bed was unnecessary, Sam responded with ‘Different strokes for different folks,’ or some shit like that.  Nothing else. If Sam had gotten any since then, Dean didn’t know about it.  All of Dean’s conquests were out of Sam’s presence. 

Dean had decided after two weeks of frantically trying to reciprocate, it would happen when it’s meant to happen. When he saw this girl from across the bar it hit him like a ton of bricks: gorgeous face, full lips, platinum blonde hair, tits that were big enough to be a handful but not overwhelming, and a nice, big ass – definitely enough to be a handful and overwhelming at the same time.  She was wearing jeans that were low and looked painted on with a form fitting long sleeve shirt; it left nothing to the imagination.  From the way she started eye-fucking him from across the room, he knew he’d be able to get her to leave with him, but if he was going to strike out on this whole Sam thing he’d rather do that at the bar.  Sam was back at the hotel saying something about research while Dean was having a few to take the edge off.  Dean made his way over to her and put on his best moves, ordered her another drink, and after downing his own he broached the subject with her. 

“What like a threesome?” She wasn’t disgusted, she looked intrigued, actually, “Depends, does he look anything like you?” She slipped her hands into Dean’s button down shirt and over the thin t-shirt underneath as she spoke.  Jackpot. 

“No, not a threesome, honey.  He’d just be watching me rock your world,” he almost laughed at the slight disappointment in her eyes, certainly a first. “But, yeah, if it matters, I guess he’s hot.  Not as hot as me, obviously!” She had to laugh at that and he leaned in close whisper filthy in her ear, “He’s taller than me though.  Huge cock.  You’d definitely be able to see it the entire time if you wanted to… what do you say? I agree to keep you facing him the whole time and make you come until you can’t see straight. We all win.” 

If life taught Dean anything: any line will work if you say it with enough confidence.  Just like that she asked for the check and he was able to grope her ass while he waited for his.  He loved how much he could dig his fingers in and make her squirm. 

* * *

 

She drove back to the motel, it was walking distance but she knew she’d be making an exit shortly afterwards.  Dean always did like the smart down-to-fuck girls for their forethought in these situations.  Dean opened the door and let her walk in first.  Sam was hunched over his laptop nursing his third beer. He perked up when someone who was very much not his brother walked in.  Dean pulled her by the hand to him and planted a quick kiss on her lips as he closed the door.  “Bathroom’s over there.  I just need to talk to my brother for a second,” he gave her a wink as she pulled away and walked to the bathroom.  She tried not to look Sam over as she walked past him but couldn’t stop herself, damn, this guy wasn’t kidding about his brother being hot too.  

“I guess I’ll wait in the car until…” Sam started. 

“No, you stay put,” Dean put an arm to Sam’s chest, “This is payback for a couple months ago little brother.” Sam looked confused. Dean awkwardly cleared his throat, “You know, a few months back…” Sam still wasn’t following.  Maybe he drank more than the two empties that were on the table. “Um… I was, uhhh, you know,” Dean made a jerking off motion with his hand and the light bulb seemed to go off in Sam’s brain, “And you came in with that brunette…” 

“So what you’re suggesting is that I stay and watch you because of a few months ago? That was a spur of the moment thing. This is… I don’t know, different.” Sam was a little flustered by it.  Dean always did have a talent for putting him into this position. 

“Come on, bitch! You afraid you might learn a thing or two?” Dean raised his eyebrows in that way that he knew he could goad Sam with and Sam took the bait. 

“Please.  You’re not the sexpert you claim to be, you know,” Sam pulled a bitchface to go with the response.  Dean had to try really hard not to laugh in his face at the word ‘sexpert.’ 

Whatever response Dean had evaporated when the bathroom door swung open and the blonde woman sauntered over to them. She pulled Dean’s face to hers in a quick, sloppy kiss before pulling away to look at Sam. “Is he staying to watch?” She ran a hand from Sam’s shoulder down to his wrist as she spoke. 

All rational thought screaming at him ceased, all the reasons why this was a bad, bad, terrible idea went out the window. The way she was looking him over told Sam that she was very into this, Dean clearly was too, and who was he to deny.  “Sure am,” Sam responded, not breaking eye contact with her. 

Dean grinned ear to ear.  “Well then get comfy, Sammy!” He pulled her hand away from Sam and put it purposefully over his denim-clad crotch. She took the hint and started rubbing him hard, “I sorta told her she could watch you while you watched us…” he broke off with a moan when she rubbed harder.  “Where this goes depends on where you want to watch from.” He stopped resisting and nipped at her plush lower lip before taking her in a forceful kiss.  She moaned into it and started pushing at his button down shirt off with her free hand. He tangled one hand in her long hair and the other started pushing up her shirt.  

Sam took off his overshirt and turned the chair he had been sitting in to face Dean’s bed.  He sat down with his legs splayed wide but made no further movement. If Dean was doing this for him then he wasn’t going to blow off early, Dean was going to have to work for it. 

Dean opened his eyes slightly in the kiss and pulled away with an aroused moan, “Mmmm, good spot Sammy.” He turned to the girl, “You know it’s his birthday this week?” 

“Really?” She was suspicious. 

“Yep, May 2nd,” he leaned close to her ear but spoke loud enough that Sam could still hear him. “You want to give him a present? How about a lap dance for his birthday? He’s sitting perfectly for it.” He gave her a firm slap on the ass to punctuate his point. 

Before Sam could move to close his legs or sit up and she in front of him.  She put a hand on his shoulder as she stood between his legs and swayed her hips. Her firm breasts were at his eye level.   She noticed where his attention was and swiftly pulled her shirt over her head.  She had a lacy, see-through bra on.  Sam didn’t really get a chance to appreciate it though; she turned to have her back to him.  She looped an arm behind his neck and ground her ass down onto his lap in slow, deliberate circles. Over her shoulder, he could see Dean had discarded his shirt too and was sitting on the bed watching as he stroked himself through his jeans.  

She kept eye contact with Dean as she gyrated on Sam. Dean spoke up, “Whatever you take off, I take off.” Sam had heard it in passing before, the Dean sex voice, but he could negotiate out of a nuclear standoff in that voice.  It was all smooth promises and lust. She cracked a smile and leaned her back against Sam’s chest for support, toeing off her heels and giving Dean a challenging stare as she resumed her motions.  Dean kept eye contact as he unlaced his boots and pulled them off along with his socks and reclined back on his elbows in challenge. 

She stood up straight and turned to face Sam again, she popped the top button of her jeans and Sam ran his hands along her hips. She playfully slapped his hands away, “No touching the dancers!” 

Dean laughed from the bed, “Yeah, haven’t you ever had a lap dance before?!” 

Sam couldn’t even focus on being annoyed because he was fascinated by the slow drag of her zipper sliding down. She hooked her thumbs into the waistband on her jeans and bent forward, breasts almost pressed to Sam’s face and butt pushed wonderfully out towards Dean.  Dean groaned as she pulled down the jeans and revealed matching sheer panties.  When she got them to her knees she dropped them and let them pool at her ankles. She stepped out of them and strode over to the bed.  Dean already had his belt unbuckled and his fly open, she decided to take over stripping them and his boxers off to the floor.  Before Dean could react she was straddling him and rubbing her panties over his erection.  He was gonna blow fast if she kept that up, he had a deep running kink for the feeling on panties on his dick.  

He grabbed her firmly by the hips and flipped them, grinding purposefully against her crotch before moving down to duck his head and suck on her nipples through the fabric of her bra.  She let out a surprised yelp as sucked and flicked his tongue over her.  He snaked a hand under her to unhook the bra and yanked it off of her, pulling back to take it off only to continue his treatment on the other side.  She was writhing under him as he peppered kisses down her stomach to the line of her panties.  He leaned down between her legs and licked her crotch over the panties.  The thin fabric did nothing to hide the effect he was having on her.  He kept his motions up, flicking his tongue over her clit and sucked down hard over it when she let out a small whine. He did everything he’d do if he would on her bare skin, but the texture was adding to what he was getting out of it.  He was going to make sure those panties were soaked through with her juices and his saliva. He kept going, swirling his tongue occasionally to get one of those high-pitched noises to punch out of her. 

Suddenly and without warning, he pulled up and went back to sucking on her breasts, nipping lightly, as he let his hand take over where his mouth was.  He could feel the ruined, wet fabric under his fingers as he rubbed back and forth over her with the just-right amount of pressure.  He could feel her fingernails digging into his skin where she held onto him and knew she was close.  He decided to continue on, flicking his wrist occasionally to make her arch up into him. He could feel her gush a little as she threw her head back and screamed.  That was when he finally pulled back and took her panties off. He rolled her hips forward bringing her legs to her chest as he licked a long stripe over her. He dipped his tongue in slightly before flicking it over her clit a few times; she pushed back against his forehead, still shaking from her orgasm.  Dean didn’t hear a ‘no’ or ‘stop’ though, so he continued his motions and finally plunged two fingers firmly into her.  He crooked them up slightly, smiling as he heard the squelching sound of his fingers inside her.  Maybe it was greedy, but he would never turn down an opportunity to make a girl come on his tongue.  He loved the heat and taste of it.  And women were like a diesel engine: once you got them going they’d go and go and go.  True to form she came again on the heels of her first orgasm.  Normally he’d give a break but he was putting on a show for his brother.  He kept going, finger fucking her through it before she shoved back against him. He took mercy and decided to give her a breather.  

When he pulled back he noticed Sam clicking on his computer.  “Dude!” Dean couldn’t help the insult and scoff in his voice. 

“What?” Sam looked back to him, “I’ll watch when you make it interesting.” Sam never could turn down an opportunity to get under his skin.  Sam picked up his beer and made a show of taking a long sip of his beer. 

Dean flipped him off as he reached down for his jeans, fumbling in the pockets for a condom.  He rolled it on and tapped the girl on the hip, “Roll over.” 

She complied flipping on her stomach and starting to get on her hands and knees.  “No,” Dean started, “Flat and legs together.” She shot him another skeptical look and Sam raised an eyebrow.  He pulled her legs so she was on an angle, facing Sam as promised.  He took a moment to knead the globes of her butt, making her moan.  He made a made a mental note that she probably likes that and continued on.  He straddled her thighs and kissed the back of her neck.  He pulled back slightly to grip his dick and rub it between her cheeks.  

She arched back and propped up on her elbows. He kept doing it until she demanded, “Stop teasing!” and moaned again as he gave her a gentle swat on the ass. 

Dean grinned and pressed up on her ass with his free hand.  “As you wish,” he purred. Then he was lining up with her pussy, being very careful in this position to not fumble into anal sex by accident, and pushing slowly in.  She let out a loud, constant moan as he forced his way in.  That was why he loved this position, it made her feel incredibly tight to him and, if his previous partners are to be believed, she was feeling filled up and stretched in the best possible way. Dean knew she was wet enough to not need an adjustment period, as soon as he was halfway in he began circling and rolling his hips forward before pushing his ass back as he pulled back then up and forward as he thrust slowly back in.  The motion was giving her stimulation on her g-spot as the head of his cock pushed back in, and the pull-drag was causing overwhelming pleasure. 

Sam watched intently.  He had shoved his jeans out of the way and pulled his boxers down just enough to free his cock.  He couldn’t help the moan that he let out when he watched the girl’s eyes roll back into her head from what Dean was doing to her.  He was torn between watching her face and the subtle jiggle of her ass as Dean plunged in and out of her.  So maybe Dean wasn’t wrong, it was definitely possible to get a girl completely fucked out without being rough, but he’d never admit that out loud.  He was enjoying watching though.  

Dean kept his motions, letting out a stray grunt here and there, until she was coming again.  Sam wasn’t sure she was going to recover from that one. Dean did the gentlemanly thing and pulled out instead of overstimulating her.  When he was confident she had ridden through her orgasm, he pulled her back onto her knees and slid in again.  Sam started stroking himself in earnest, enjoying how completely lost to pleasure this woman was.  Dean kept his same even pace pumping in and out of her as he let his hands wander and touch any free skin he could get his hands on. When he decided he was going for the big finish, he pulled her up off the bed against his chest. She let out a shocked moan and was practically boneless against him.  He kept one arm locked around her waist as he sucked on her neck, continuing his thrusting. 

From this angle Sam could see everything, he was focused on Dean’s dick plunging into her and coming out slick and shiny. Her juices from previous orgasms were dripping on Dean’s legs slightly and definitely all over her thighs. He shouldn’t have looked, now he was completely transfixed and Dean probably knew it.  Dean thrust up into her hard three times before slowing his pace again, grinning when he heard his brother let out another long groan. He reached his free hang down to ghost over her stomach to go between her legs.  All it took was a few flicks of his fingers over her clit and he heard Sam coming.  It didn’t take much more after that and she was coming too, her scream choking off into a hoarse sound.  Dean thrust a few more times and let himself go too, griping her tightly to him so she could feel his muscles lock up. 

Dean had the good conscious to gingerly lay her down before collapsing back with a thud.  He panted for a moment before he grinned and rolled his head to ask her, “You good? Or do you need another one?” 

“Holy shit,” was the panted out response he got. Her hair was a mess, makeup smeared, lips swollen, completely lax and blissed out body sprawled out where he left her. “That.  Was amazing.” 

Sam cleaned himself up a little with a napkin from the table before giving up and going to the bathroom to clean up. He wouldn’t admit it to Dean but he was so entranced in what Dean was doing to her that he forgot to take his own shirt off, resulting in a jizz mess all over his shirt and jeans. He didn’t have the luxury of leaving it until whenever they did laundry, so he was going to get the worst of it off his clothes. 

When he finally emerged from the bathroom the girl was gone and Dean was in his boxers and retrieving his shirt from the floor. He turned to Sam and gave one of his flirty, megawatt smiles, “You’re welcome.”

**Author's Note:**

> Inspiration came from this gif. I was struggling on writing not-rough sex for Dean because of the events in the first story.  
> 
> 
> Edit: it occurred to me that I *really* should have been crediting the original posts of gifs. No one said anything, but if one were looking for more of the same I found this one here:  
> Like to watch 2 credit   
> http://mysterywriteher.tumblr.com/post/105278911422/i-will-find-your-spot-and-nail-it-until-your-eyes  
> (One of the best 18+ blogs on Tumblr, FYI)


End file.
